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Heterolytic Alkyl Hydroperoxide O–O Bond Cleavage by Copper(I) Complexes
Author(s) -
Tano Tetsuro,
Sugimoto Hideki,
Fujieda Nobutaka,
Itoh Shinobu
Publication year - 2012
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201200555
Subject(s) - heterolysis , chemistry , homolysis , bond cleavage , cumene , acetophenone , cumene hydroperoxide , copper , peroxide , alkyl , cleavage (geology) , stoichiometry , medicinal chemistry , photochemistry , ketone , polymer chemistry , organic chemistry , catalysis , radical , geotechnical engineering , fracture (geology) , engineering
The reaction of copper(I) complexes and cumene hydroperoxides was examined to demonstrate that heterolytic O–O bond cleavage of the peroxides proceeds predominantly to give the corresponding alcohols (cumyl alcohols) as the major product, when the stoichiometry of Cu I /peroxide is 2:1. The result is in sharp contrast to the 1:1 reaction between the copper(II) complexes and cumene hydroperoxide, which provides the ketone (acetophenone) as the major product through homolytic O–O bond cleavage.